Cesium carbonate → Tert-butyl (3R)-3-[[5-(5-cyclopropyl-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

HRID 1507540Notes

Reaction equation

HRID 1507540 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]3[S:11][CH:10]=[N:9][C:8]=3[CH:12]=2)[CH2:3][CH2:2]1.I[C:14]1[C:15]([NH:28][C@@H:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]2)=[N:16][C:17]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[N:18][C:19]=1[O:20][CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]3[S:11][C:10]([C:14]4[C:15]([NH:28][C@@H:29]5[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]5)=[N:16][C:17]([N:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)=[N:18][C:19]=4[O:20][CH3:21])=[N:9][C:8]=3[CH:12]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 895452295-Cyclopropyl-1,3-benzothiazoleHCID 89554305(R)-Tert-butyl 3-(5-iodo-6-methoxy-2-morpholinopyrimidin-4-ylamino)piperidine-1-carboxylate

Product 1

HCID 117683817Tert-butyl (3R)-3-[[5-(5-cyclopropyl-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Following the same procedure as in step 3 of Example 337 using 5-cyclopropyl-1,3-benzothiazole (61.4 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100 mg, 0.19 mmol, 1.00 equiv), cesium carbonate (0.37 g, 6.00 equiv, 1.14 mmol), Pd(PPh3)4 (40.4 mg, 0.035 mmol, 0.18 equiv) and copper iodide (6.7 mg, 0.035 mmol, 0.18 equiv) in DMF (6.0 mL). The crude product was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (20:1-5:1) to provide the title compound as a white solid. MS m/z [M+H]+ (ESI): 567.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with petroleum ether/ethyl acetate (20:1-5:1)

Sources & evidence

ORD record
ord-5e5bb4487eaf418ea177f7484e76ef05
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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